


Not Meant to Fight Dirty

by SinOfPride



Category: Supernatural
Genre: F/M, Other, Pre-Canon, Schmoop, Sexual Identity, Teenage Winchesters, Trans Female Character
Language: English
Status: Completed
Published: 2012-02-11
Updated: 2012-02-11
Packaged: 2017-10-30 23:35:10
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,966
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/337412
Author URL: https://archiveofourown.org/users/SinOfPride/pseuds/SinOfPride
Summary: <blockquote class="userstuff">
              <p>Dean didn't know what he saw in her at first.</p>
            </blockquote>





	Not Meant to Fight Dirty

**Author's Note:**

> Title's from the Marina and the Diamonds song _Girls_. Self indulgent Dean-centric schmoop.

Dean didn't know what he saw in her at first. 

She was a quiet girl that wore baggy clothes to hide her body, the sort to hide in the back of the classrooms and half-smile if someone was nice to her, duck her head if they weren't. She rarely made eye-contact and wore thin red glasses, which he thought made her look smart. Usually that was the type Dean avoided because, well- when had Dean ever been accused of being smart? Charming, sure, quick on his feet, but brains were Sammy's thing. And smart girls tended to stay well away from the likes of him.

All in all, she was unremarkable from a thousand other mousy girls at a dozens different schools he'd been through before. 

Except for how she wasn't.

Except for how she looked at Dean like she thought he was plenty smart and only laughed off the crude jokes and clumsy advances that usually worked on the easy girls. Those girls, the ones that looked at his attitude and thought 'bad boy', good enough for some meaningless fun, those were usually the only ones to give him the time of day. 

But Jen-- not her. She was completely different.

Jen looked at Dean and actually saw him. When he sat next to her in class, she'd blush and smile like him being there was good enough, like he didn't have to try so hard to seem like someone she'd want. She talked to him like what he said was important and always asked for his opinion like it mattered to her. 

She would let Dean borrow her notes without calling him stupid and always went on about their English assignments in ways that made them seem surprising and new. Jen made him want to read everything just so he could talk about the books with her over lunch. 

"He's a manifestation of modern society!" She'd say, pulling up her glasses and sliding over half of her sandwich when she saw Dean didn't have one. 

They'd been short on cash at home again. Dean tried to give it back, but Jen ignored him, green eyes intent on getting his take of Catcher in Rye.

"Holden represents those dark impulses, the need to disregard society's rules, you know? He wants to be a bad seed." She'd insisted, sipping her water.

"He's a dick," Dean had said, munching on the best damn meatloaf sandwich he'd ever had and trying not to look too desperate as he wolfed it down. 

He probably didn't succeed, 'cause Jen wordlessly handed him a Sneakers bar from her disconcertingly large book bag, which was always overflowing. Dean didn't know why she even had a locker when she carried everything around all day. 

"And a clueless idiot that thinks he's so sharp." Dean said, tearing into the chocolate. He got a kick out of her pout. "He’s still a virgin! I disregard society's rules every day without being a loser about it." 

"You might find people who'd disagree with that assessment," She'd said, smirking through a blush. With anyone else Dean would have taken offense, but not with her. She'd laughed like she didn't believe that for a minute. 

Dean had never had that ease with anyone except for Sammy and even then, his brother had a mean streak a mile wide. 

Dean just grinned cockily at her, faintly hoping he didn't have chocolate in his teeth. 

He'd never read so many books in so short a time, just trying to keep up with her. She knew it too and always looked mischievous when she brought out a new one, reading him bits of it, talking about the characters like they were real people. 

Dean thought she'd get along great with his geeky little brother, but Sammy was a total ass when he met her. He barely spoke two words, glaring under his hair when he thought Dean wasn't looking, playing the bitchy brat to a tee. Jen played it cool, but Dean knew the kid had made her uncomfortable. When Dean told him off for it, Sam told Dean he thought Jen was kind of a freak and why was Dean with her all the time anyway? Dean gave him the cold shoulder for two days. 

Jen wasn't a freak. If anything, that was Dean. Jen might be shy, but she was smart and fun. Her nose had the cutest little freckles, which- while on himself he hated, they did nothing for Dean's hard earned tough image - he thought made her look beautiful in the sunlight. 

After a while, Dean took to trailing her around school most of the time. When he asked her about other friends, Jen confided she was also new and didn't know many people. 

Dean thought other girls were mean to her, shunning her out, but high-school hierarchy was ridiculous like that. Jen let herself fade to the background with her hidden curves, second-hand clothes and dirty blond hair always in her eyes. Even so, Dean would rather hang out with her over the large-breasted girls wearing their jock boyfriend's varsity jackets like a badge of honor. Jen was soft-spoken but _funny_ , with a wit about her that made everyone else at school seem dull in comparison. 

So Dean made sure to clear the way for her in the halls and carried her stupidly heavy bag over her protests. 

On his first day, Jen had approached him to mumble that she liked his notebook, decorated as he had it with band stickers and car pictures. He'd made her laugh when he said he had to try and make what was inside look half-interesting, but she'd said they shared a math class and he could play dumb all he wanted but he'd solved that last equation faster than anyone else. 

From then on Dean had made an effort, side-stepping the cheerleaders that tried to lure him to the football field, to sit with Jen at lunch and ask her about Shakespeare. 

Jen was special.

So maybe he stepped up his game a little too. Maybe he read those books because she made them sound special and because he wanted to talk to her, but also because he didn't want to disappoint her. Dean didn't want to be his usual dumb self or seem too boring to someone with a mind like hers. She liked him and Dean didn't want that to stop. He thought maybe, if he was smart enough, he could be someone she could maybe date. 

Whatever. There wasn't anything wrong with wanting that. 

Jen was cute. Her eyes were very green and her smile was gorgeous, but rare, so he made an effort to see it every day. 

He may or may not have started wearing aftershave sometimes, despite Sam's smirk. 

And maybe he could have eaten lunch a few more times instead of taking her to that geeky horror film screening she'd wanted to see. Or buying her that Spanish poetry book she'd been coveting for her birthday. 

It was also possible he didn't _have_ to pay for her soda and popcorn that one time, but he told her he wanted to pay her back for all those shared sandwiches. Jen seemed to be onto him, if her blush was any indication, but she let him do it.

Dean was not too proud to admit to being over the moon just from that, despite nothing else happening.

Then Dad told Dean there was another hunt in the area and they weren't leaving yet, possibly not for a while with the holidays coming up and all. Dad had looked a little amused over Dean's immediate smile, but Dean manfully ignored his old man ruffling his hair to start planning his next move. 

Jen loved the mixtape he made her, despite the crappy radio Dean had recorded it on and the weird song mix that went from Def Leppard to The Beatles, right through Metallica's softer side. In return she gave him one of her notebooks, filled with stories she'd written herself and an original Ozzy Osbourne tape. 

Dean thought he was in love. 

While she carefully gauged his reaction to her gifts, Dean had stared back and thought her pretty eyes looked dull behind her glasses, so he pulled them off her nose to see them better; it was a stupid impulse, since he knew she was almost blind without those. But she was right there within reach and Dean had wanted to see all of her, because it was important. It felt important. 

He'd leaned down then, expecting her to brush him off again, expecting her to laugh it off. Of course, she didn't do any of that; always bent on surprising him, Jen kissed him right back. 

Sammy teased the crap out of him when he caught Dean holding hands with Jen on the way back from school. He told Dean he'd looked like an idiot with that goofy smile, but Dean barely even heard him (though he did call Sam a little bitch, it was the principle of it). He was happy. 

Jen was awesome and she liked him back and she sat with him on the porch steps and told him they _should totally ditch class tomorrow and go for a drive, how about it?_ According to her, they could read The Great Gatsby and understand more of it without Mr. Steinbeck's squeaky commentary. Jen said _hell, we're both smarter than him anyway_. 

Dean just smiled and found Jen looking at him like he was exactly who she wanted to be with in that moment, in all the moments after.

Dean knew he was in love. 

They were together all the time; they kissed, they held hands, they went everywhere together. Dean loved when he could convince her to sit on his lap, even if she squirmed nervously the entire time and hid her face on his neck.

There was just one thing. 

They didn't go any further than that. And Dean wanted to. He wanted Jen. Dean wanted to know what it was like to move inside her, to look down and see her there, naked and flushed and smiling and _his_ in every way. Dean wanted to taste the best thing to ever happen to him, this girl who looked at him and didn't find him lacking. 

But Jen was shy. 

She kissed Dean back, held his hand and sat on his lap. She kissed his neck, ran fingers through his hair, kissed his face, nibbled on his ear, licked his chest, ran her hands over his skin with affection and excitement. But Jen wouldn't let him reciprocate. Dean wasn't allowed to touch her that way. She stopped his hands from roaming too far, smiled that little sad smile Dean hated, the one that said she felt like she was failing Dean by not saying yes. So, Dean didn't push. 

Or tried not to, anyway. He was sixteen. Sometimes it was hard to remember that this girl he loved so much didn't want him that way, not in the same wholesome way he wanted her. 

It lasted two perfect months. Jen was his girlfriend for two months. 

It was two months of the most exhilarating high Dean had ever experienced, even better than killing that werewolf on his last birthday had been. At the same time, it was two months of the most painful sexual frustration of his _life_. 

But Dean was still happy. Jen made him happy and he told her so, sitting on her bed watching a movie while her parents were out, her head on his shoulder and her hand on his chest. 

"You make me happier than I've ever been," She answered, voice hushed and Dean smiled, feeling proud. He gently ran his hand up and down the curve of her back, squeezing her body a little tighter to his, because no one had ever said that. That he made them happy. 

"You're amazing." She said and Dean laughed, went to make a joke, but she cut him off, choking out the words like they hurt. "You're the most wonderful guy I've ever met. I love you. I love you and I'm sorry I did this. I'm sorry I lied, Dean, I'm so sorry-" 

Suddenly, Dean realized she was crying. Right there in his arms, clutching his T-shirt in a death grip and crying like her heart was breaking. 

Dean panicked. He had no idea what was wrong. He was terrified he'd screwed everything up, somehow. He'd thought things between them were great- if frustrating- but Jen was crying. Dean didn't know what to do with himself to fix whatever it was. 

"Jen?" Dean whispered, bewildered. He felt her hand on his neck, clutching him close like he'd vanish any second now. "Jenny, what is it? Baby? You don't have anything to be sorry for." 

She just cried harder, her hand seeking his. Then she was moving Dean's hand, moving it down her body in a purposeful way she'd always avoided- it made no freaking sense. She was still crying. Dean went to take his hand back but her grip was like iron and Jen dragged his fingers to touch her stomach, riding up her shirt and her bra and- 

Dean frowned, feeling nothing where there should be a swell of flesh. 

Dean drew back a little, but Jen was hiding her face in his neck. Her hand was still guiding his over her flat skin. Maybe she was self-conscious? Dean opened his mouth to reassure her that he didn't _care_ about her breasts being small, or underdeveloped, or whatever it was that had her crying like this. But then she was moving his hand lower down her body, guiding it lower to pull it down her pants, to feel- 

Dean's eyes widened, fingers closing over hot flesh tightly bound by what felt like cloth, but unmistakable on touch. 

A boy. Jen was a boy? 

Jen was still mumbling broken up apologies and begging forgiveness and saying she was- he was? no, she was - so sorry, but Dean was so beautiful, so sweet and loving and everything she'd ever wanted and she couldn't tell him the truth, couldn't, she'd tried. But she was sorry, she couldn't do this to him anymore and she'd understand if Dean wanted to end it. 

"Please don't hate me. Dean, don't hate me, don't hate me- " Jen was sobbing, her other hand still clutching Dean's neck. 

Dean's mind was kind of stuck on a loop of _wait. what?_ that really wasn't helping at fucking all.

"Shh," Dean finally managed when the lump in his throat got unstuck, when he blinked back to himself to realize that- that- well, this was still Jen. 

Jen who was beautiful and wore baggy clothes with red little glasses, who talked softly and held his hand and thought Dean was smart. Jen, who had the cutest little freckles and the softest mane of hair and smiled at Dean like she couldn't believe Dean was for real. 

"Jen. Jenny, shh," Dean soothed, gently extracting his hand from where Jen still held it against the evidence of why they'd only ever kissed. Why that sad smile showed up whenever Dean forgot himself and aimed for more. Why Jen was so shy and so awkward and trying to slip under the radar.

Jen had a boy's body. But Jen dressed like a girl, acted like a girl, and she'd never lied to Dean just because her body didn't agree. 

"I could never hate you," Dean whispered fiercely and he meant that. Every word. He clutched Jen tighter and did his best to calm the sobbing, the shaking and the apologies, murmuring assurances that sounded truer every time Dean repeated them. 

Jen, his Jenny, was still the same person Dean loved, and Dean didn't love easy. And he didn't love in halves. 

"I don't care," Dean whispered into that upturned ear. He met Jen's red-rimmed, incredulous eyes with his, feeling his heart speed up on his chest like every other time Jen had looked at him like Dean was her entire world. 

"You're not gay," Jen whispered, choking out the words.

Dean wasn't. He'd never even thought about it. But if Dean thought about it, nothing had changed - this was Jen. Whatever her body looked like, Jen was his girl

"I don't care." Dean said. He could see how Jen was hanging onto every word, so Dean turned his voice into the tone he only ever used to soothe Sammy from nightmares. "You're still the same person. The same brilliant Jenny that makes me read poetry and laughs at my jokes. And you know what?" Dean said, and maybe he was a little choked up too, but Dean wasn't admitting to anything. He just brushed those tears away from Jen's face and kissed her forehead. "You're gorgeous." 

It lasted two perfect months, Jen being his girlfriend. After that, it lasted seven more months of Jensen, who said she hadn't settled on a new name just yet, being his girl.

And when they finally had to leave- because they had to, because Dad couldn't put it off any longer and looked honestly pained to have to tell Dean as much- Jensen told Dean he loved him. She told Dean he'd wait. Told him that if it took forever and a day, she'd wait. 

And maybe that was Dean's thing. That thing he never told Sam about, that Dad found out by accident but was never talked about explicitly beyond a fatherly pat on the back and a smile that said it was okay. Maybe that was why Dean always, every year, went back to Virginia for as much time as he could spare.

Maybe. But that's a story for later.


End file.
